Download PDF
Synthesis 2008(21): 3487-3491  
DOI: 10.1055/s-0028-1083184
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Chemoselective Etherification of Benzyl Alcohols Using 2,4,6-Trichloro-1,3,5-triazine and Methanol or Ethanol Catalyzed by Dimethyl Sulfoxide

Lili Sun, Yuping Guo, Guisheng Peng, Chunbao Li*
Department of Chemistry, College of Science, Tianjin University, 300072 Tianjin, P. R. of China
Fax: +86(22)27403475; e-Mail: lichunbao@tju.edu.cn;
Further Information

Publication History

Received 4 June 2008
Publication Date:
16 October 2008 (online)

    Permissions and Reprints All articles of this category

Abstract

An efficient method for the transformation of benzyl alcohols into their methyl or ethyl ethers has been established using 2,4,6-trichloro-1,3,5-triazine (TCT) and dimethyl sulfoxide in methanol or ethanol. This procedure chemoselectively converts benzylic hydroxys into their methyl or ethyl ethers in the presence of aliphatic or phenolic hydroxys.

Key words

benzyl alcohols - chemoselectivity - ethers - sulfoxide - 2,4,6-trichloro-1,3,5-triazine

    References

  • 1 Larock RC. In Comprehensive Organic Transformations   2nd ed., Vol. 2:  John Wiley & Sons; Indianapolis: 1999.  p.889 
    Google Scholar
  • 2a Hutchins RO. Taffer IM. J. Org. Chem.  1983,  48:  1360 
    Google Scholar
  • 2b The Chemistry of the Ether Linkage   Patai S. Interscience; New York: 1967.  p.445 
    Google Scholar
  • 3a Ohno K. Nishiyama H. Nagase H. Tetrahedron Lett.  1979,  20:  4405 
    Google Scholar
  • 3b Caserio MC. Roberts JD. Neeman M. Johnson WS. J. Am. Chem. Soc.  1958,  80:  2584 
    Google Scholar
  • 4a Overman LE. Ricca DJ. Tran VD. J. Am. Chem. Soc.  1993,  115:  2042 
    Google Scholar
  • 4b Evans DA. Ratz AM. Huff BE. Sheppard GS. Tetrahedron Lett.  1994,  35:  7171 
    Google Scholar
  • 5a Curtin DY. Leskowitz S. J. Am. Chem. Soc.  1951,  73:  2630 
    Google Scholar
  • 5b Norris JF. Rigby GW. J. Am. Chem. Soc.  1932,  54:  2088 
    Google Scholar
  • 5c Smith HA. Smith RJ. J. Am. Chem. Soc.  1948,  70:  2400 
    Google Scholar
  • 6a Kim S. Chung KN. Yang S. J. Org. Chem.  1987,  52:  3917 
    Google Scholar
  • 6b De Mico A. Margarita R. Piancatelli G. Tetrahedron Lett.  1995,  36:  2679 
    Google Scholar
  • 6c Salehi P. Iranpoor N. Behbahani FK. Tetrahedron  1998,  54:  943 
    Google Scholar
  • 7 Jenner G. Tetrahedron Lett.  1988,  29:  2445 
    CrossrefGoogle Scholar
  • 8 Emert J. Goldenberg M. Chiu GL. Valeri A. J. Org. Chem.  1977,  42:  2012 
    CrossrefGoogle Scholar
  • 9 Traynellis VJ. Hergenrother WL. Hanson HT. Valicenti JA. J. Org. Chem.  1964,  29:  123 
    Google Scholar
  • 10 Lange NA. In Handbook of Chemistry   9th ed.:  Handbook Pubs. Inc.; Sandusky: 1956.  p.1222 
    Google Scholar
  • 11 Edsall AB. Mohanakrishnan AK. Yang D. Fanwick PE. Hamel E. Hanson AD. Agoston GE. Cushman M. J. Med. Chem.  2004,  47:  5126 
    CrossrefPubMedGoogle Scholar
  • 12 Peters RH. Chao W.-R. Sato B. Shigeno K. Zaveri NT. Tanabe M. Steroids  2003,  68:  97 
    CrossrefPubMedGoogle Scholar
  • 13 Lovely CJ. Gilbert NE. Liberto MM. Sharp DW. Lin YC. Brueggemeier RW. J. Med. Chem.  1996,  39:  1917 
    CrossrefPubMedGoogle Scholar
  • 14 Kumar HMS. Anjaneyulu S. Joyasawal S. Chakravarthy PP. Kumar VN. Yadav JS. J. Indian Chem. Soc.  2007,  84:  189 
    Google Scholar
  • 15 Kirmse W. Konrad W. Oezkir IS. Tetrahedron  1997,  53:  9935 
    CrossrefGoogle Scholar
  • 16 Srikrishna A. Viswajanani R. J. Indian Chem. Soc.  2000,  77:  621 
    Google Scholar
  • 17 Dem’yanovich VM. Khlebnikov VA. Russ. J. Org. Chem.  1994,  30:  255 
    Google Scholar
  • 18 Malkov AV. Baxendale IR. Dvořak D. Mansfield DJ. Kočovský P. J. Org. Chem.  1999,  64:  2737 
    CrossrefPubMedGoogle Scholar
  • 19 Selivanov BA. Bil’kis II. Shteingarts VD. J. Org. Chem. USSR (Engl. Trans.)  1992,  28:  1357 
    Google Scholar
  • 20 Hurd CD. Iwashige T. J. Org. Chem.  1959,  24:  1321 
    CrossrefGoogle Scholar
  • 21 Cook SP. Danishefsky SJ. Org. Lett.  2006,  8:  5693 
    CrossrefPubMedGoogle Scholar